diff --git a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/attribute.py b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/attribute.py
index 6312b607d5c1e1..6f5a7ac1a60d89 100644
--- a/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/attribute.py
+++ b/crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/attribute.py
@@ -152,3 +152,20 @@
     f(111111111111111111111111111111111111111111111111111111111111111111111111111111111)
     + 1
 ).bit_length()
+
+
+# Regression test for https://github.com/astral-sh/ruff/issues/16151
+result = (
+   (await query_the_thing(mypy_doesnt_understand))  # type: ignore[x]
+   .foo()
+   .bar()
+)
+
+(
+    (
+        a # trailing end-of-line
+        # trailing own-line
+    ) # trailing closing parentheses
+    # dangling before dot
+    .b # trailing end-of-line
+)
diff --git a/crates/ruff_python_formatter/src/comments/placement.rs b/crates/ruff_python_formatter/src/comments/placement.rs
index 8c8744f970e7a1..cf5316af5be773 100644
--- a/crates/ruff_python_formatter/src/comments/placement.rs
+++ b/crates/ruff_python_formatter/src/comments/placement.rs
@@ -1391,10 +1391,8 @@ fn handle_attribute_comment<'a>(
         .take_while(|token| token.kind == SimpleTokenKind::RParen)
         .last()
     {
-        return if comment.start() < right_paren.start() {
-            CommentPlacement::trailing(attribute.value.as_ref(), comment)
-        } else {
-            CommentPlacement::dangling(comment.enclosing_node(), comment)
+        if comment.start() < right_paren.start() {
+            return CommentPlacement::trailing(attribute.value.as_ref(), comment);
         };
     }
 
diff --git a/crates/ruff_python_formatter/src/expression/expr_attribute.rs b/crates/ruff_python_formatter/src/expression/expr_attribute.rs
index fd70c3d2d498f7..6d3555f7eb9968 100644
--- a/crates/ruff_python_formatter/src/expression/expr_attribute.rs
+++ b/crates/ruff_python_formatter/src/expression/expr_attribute.rs
@@ -1,7 +1,7 @@
 use ruff_formatter::{write, FormatRuleWithOptions};
 use ruff_python_ast::AnyNodeRef;
 use ruff_python_ast::{Expr, ExprAttribute, ExprNumberLiteral, Number};
-use ruff_python_trivia::{find_only_token_in_range, SimpleTokenKind};
+use ruff_python_trivia::{find_only_token_in_range, SimpleTokenKind, SimpleTokenizer};
 use ruff_text_size::{Ranged, TextRange};
 
 use crate::comments::dangling_comments;
@@ -50,9 +50,6 @@ impl FormatNodeRule<ExprAttribute> for FormatExprAttribute {
                 if parenthesize_value {
                     // Don't propagate the call chain layout.
                     value.format().with_options(Parentheses::Always).fmt(f)?;
-
-                    // Format the dot on its own line.
-                    soft_line_break().fmt(f)?;
                 } else {
                     match value.as_ref() {
                         Expr::Attribute(expr) => {
@@ -60,11 +57,9 @@ impl FormatNodeRule<ExprAttribute> for FormatExprAttribute {
                         }
                         Expr::Call(expr) => {
                             expr.format().with_options(call_chain_layout).fmt(f)?;
-                            soft_line_break().fmt(f)?;
                         }
                         Expr::Subscript(expr) => {
                             expr.format().with_options(call_chain_layout).fmt(f)?;
-                            soft_line_break().fmt(f)?;
                         }
                         _ => {
                             value.format().with_options(Parentheses::Never).fmt(f)?;
@@ -77,19 +72,56 @@ impl FormatNodeRule<ExprAttribute> for FormatExprAttribute {
                 value.format().with_options(Parentheses::Never).fmt(f)?;
             }
 
+            let comments = f.context().comments().clone();
+
+            // Always add a line break if the value is parenthesized and there's an
+            // end of line comment on the same line as the closing parenthesis.
+            // ```python
+            // (
+            //      (
+            //          a
+            //      )  # `end_of_line_comment`
+            //      .
+            //      b
+            // )
+            // ```
+            let has_trailing_end_of_line_comment =
+                SimpleTokenizer::starts_at(value.end(), f.context().source())
+                    .skip_trivia()
+                    .take_while(|token| token.kind == SimpleTokenKind::RParen)
+                    .last()
+                    .is_some_and(|right_paren| {
+                        let trailing_value_comments = comments.trailing(&**value);
+                        trailing_value_comments.iter().any(|comment| {
+                            comment.line_position().is_end_of_line()
+                                && comment.start() > right_paren.end()
+                        })
+                    });
+
+            if has_trailing_end_of_line_comment {
+                hard_line_break().fmt(f)?;
+            }
+            // Allow the `.` on its own line if this is a fluent call chain
+            // and the value either requires parenthesizing or is a call or subscript expression
+            // (it's a fluent chain but not the first element).
+            else if call_chain_layout == CallChainLayout::Fluent {
+                if parenthesize_value || value.is_call_expr() || value.is_subscript_expr() {
+                    soft_line_break().fmt(f)?;
+                }
+            }
+
             // Identify dangling comments before and after the dot:
             // ```python
             // (
             //      (
             //          a
-            //      )  # `before_dot`
+            //      )
             //      # `before_dot`
             //      .  # `after_dot`
             //      # `after_dot`
             //      b
             // )
             // ```
-            let comments = f.context().comments().clone();
             let dangling = comments.dangling(item);
             let (before_dot, after_dot) = if dangling.is_empty() {
                 (dangling, dangling)
diff --git a/crates/ruff_python_formatter/tests/snapshots/format@expression__attribute.py.snap b/crates/ruff_python_formatter/tests/snapshots/format@expression__attribute.py.snap
index b0f564cacd3b79..89ce7d237b16d2 100644
--- a/crates/ruff_python_formatter/tests/snapshots/format@expression__attribute.py.snap
+++ b/crates/ruff_python_formatter/tests/snapshots/format@expression__attribute.py.snap
@@ -1,7 +1,6 @@
 ---
 source: crates/ruff_python_formatter/tests/fixtures.rs
 input_file: crates/ruff_python_formatter/resources/test/fixtures/ruff/expression/attribute.py
-snapshot_kind: text
 ---
 ## Input
 ```python
@@ -159,6 +158,23 @@ result = (
     f(111111111111111111111111111111111111111111111111111111111111111111111111111111111)
     + 1
 ).bit_length()
+
+
+# Regression test for https://github.com/astral-sh/ruff/issues/16151
+result = (
+   (await query_the_thing(mypy_doesnt_understand))  # type: ignore[x]
+   .foo()
+   .bar()
+)
+
+(
+    (
+        a # trailing end-of-line
+        # trailing own-line
+    ) # trailing closing parentheses
+    # dangling before dot
+    .b # trailing end-of-line
+)
 ```
 
 ## Output
@@ -295,4 +311,21 @@ result = (
     f(111111111111111111111111111111111111111111111111111111111111111111111111111111111)
     + 1
 ).bit_length()
+
+
+# Regression test for https://github.com/astral-sh/ruff/issues/16151
+result = (
+    (await query_the_thing(mypy_doesnt_understand))  # type: ignore[x]
+    .foo()
+    .bar()
+)
+
+(
+    (
+        a  # trailing end-of-line
+        # trailing own-line
+    )  # trailing closing parentheses
+    # dangling before dot
+    .b  # trailing end-of-line
+)
 ```